The Rocca di Radicofani, with documents attesting to its existence as far back as 978, reveals its ancient origins dating back to the Carolingian era. Its strategic position along the ancient Via Francigena made it essential for the Monks of Abbadia San Salvatore and later for the control of the territory by the Papal State and the Republic of Siena.

The exploits of Ghino di Tacco, known as the Italian Robin Hood, give the Rocca di Radicofani legendary fame in the 13th century. Ghino, a gentleman bandit, seizes the fortress twice between 1297 and 1300, becoming a rebellious Ghibelline figure celebrated even by Dante and Boccaccio.

The Rocca undergoes various changes of ownership and conflicts until it becomes the definitive possession of the Republic of Siena in the 15th century. Transformed into a fortress in the 16th century under the Grand Duchy of Tuscany, its pentagonal structure and imposing defenses testify to its strategic importance. Destroyed in 1735 and subsequently restored, today the Rocca di Radicofani offers a spectacular view of the Valdorcia and remains a tangible symbol of Tuscan history and resistance.
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